4-(2-Acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide → (2S,5R)-4-(2-acetamidoethyl)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627258Notes

Reaction equation

HRID 627258 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:13]2[CH2:14][N:10]([C:11](=[O:23])[N:12]2[O:15]CC2C=CC=CC=2)[CH:9]([C:24]([NH2:26])=[O:25])[CH:8]=1)(=[O:3])[CH3:2].C(NCCC1[C@@H]2CN(C(=O)N2OCC2C=CC=CC=2)[C@H](C(N)=O)C=1)(=O)C>CCOC(C)=O.C(O)C.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C@@H:13]2[CH2:14][N:10]([C:11](=[O:23])[N:12]2[OH:15])[C@H:9]([C:24]([NH2:26])=[O:25])[CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 898525004-(2-Acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideHCID 89863102(2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

Product 1

HCID 89852077(2S,5R)-4-(2-acetamidoethyl)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideYield 101.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 247, 0.120 g, 0.33 mmol) in EtOAc (20 mL) and ethanol (6.67 mL) was added Pd/C (0.036 g, 0.33 mmol). The reaction mixture was stirred under hydrogen at 1 atm for 1 hour, then filtered through celite and concentrated to dryness to afford the title compound as a white solid (0.09 g, 100%).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7b2b6ba395cc4a35818b90a1cabd906f
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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